JPH0765066B2 - Method for producing eicosapentaenoic acid-containing substance using red alga Fudarac - Google Patents
Method for producing eicosapentaenoic acid-containing substance using red alga FudaracInfo
- Publication number
- JPH0765066B2 JPH0765066B2 JP4195829A JP19582992A JPH0765066B2 JP H0765066 B2 JPH0765066 B2 JP H0765066B2 JP 4195829 A JP4195829 A JP 4195829A JP 19582992 A JP19582992 A JP 19582992A JP H0765066 B2 JPH0765066 B2 JP H0765066B2
- Authority
- JP
- Japan
- Prior art keywords
- eicosapentaenoic acid
- fudarac
- red alga
- containing substance
- extraction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 235000020673 eicosapentaenoic acid Nutrition 0.000 title claims description 20
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 title claims description 16
- 229960005135 eicosapentaenoic acid Drugs 0.000 title claims description 16
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 title claims description 16
- 239000000126 substance Substances 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000000605 extraction Methods 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 241001474374 Blennius Species 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 2
- 241000199919 Phaeophyceae Species 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- 150000001746 carotenes Chemical class 0.000 description 2
- 235000005473 carotenes Nutrition 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000512259 Ascophyllum nodosum Species 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241000195628 Chlorophyta Species 0.000 description 1
- 241000206572 Rhodophyta Species 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 108020001775 protein parts Proteins 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】Detailed Description of the Invention
【０００１】[0001]
【産業上の利用分野】本発明は、これまであまり返り見
られなかった未利用海藻である紅藻フダラクより血清脂
質改善作用や血液凝固抑制作用などを有するエイコサペ
ンタエン酸含有物質を製造する方法に関するものであ
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an eicosapentaenoic acid-containing substance having a serum lipid-improving action and a blood coagulation-inhibiting action from the red seaweed Fudarac, an unused seaweed that has not been frequently returned. It is a thing.
【０００２】[0002]
【従来の技術】エイコサペンタエン酸（以下ＥＰＡとい
う）は血栓症、脳梗塞、心筋梗塞等を防止する作用のあ
ることで知られているが、ＥＰＡ等の高度不飽和の高級
脂肪酸は体内で形成されない。このような高級高度不飽
和脂肪酸の供給原料としては肝油など魚類等がその主な
ものである。供給原料の拡大として、未利用海洋バイオ
マス資源の利用が考えられるが、海洋に植生する、日本
近海でも千数百種という極めて多種類にのぼり、大きく
は褐藻類、緑藻類、紅藻類に大別される海藻について
は、コンブのような褐藻類のうちのわずかのものしかそ
の有効利用がないのが現状である。2. Description of the Related Art Eicosapentaenoic acid (hereinafter referred to as EPA) is known to have an action of preventing thrombosis, cerebral infarction, myocardial infarction, etc., but highly unsaturated higher fatty acids such as EPA are formed in the body. Not done. As a feedstock for such higher polyunsaturated fatty acids, fish such as liver oil are the main ones. The use of unused marine biomass resources can be considered as an expansion of raw materials to be supplied, but the number of species in the oceans near Japan, which exceeds 100,000 species, is extremely large, and is broadly divided into brown algae, green algae, and red algae. Currently, only a few of the brown algae such as kelp are used effectively.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、このような
事情の下、未利用海藻からエイコサペンタエン酸含有物
質を工業的に効率よく製造する方法を提供することを目
的としてなされたものである。Under such circumstances, the present invention has been made for the purpose of providing a method for industrially and efficiently producing a substance containing eicosapentaenoic acid from unused seaweed. .
【０００４】[0004]
【課題を解決するための手段】本発明者らは、未利用海
藻からエイコサペンタエン酸の工業的製造方法を開発す
るために鋭意研究を重ねた結果、極めて多種類の海藻の
中から、これまで全くＥＰＡのような高級高度不飽和脂
肪酸の含有の知られていなかった紅藻フダラクに、この
ＥＰＡが主要な脂質構成成分として存在していること、
そしてエイコサペンタエン酸含有物質を、この紅藻フダ
ラクに有機溶媒抽出あるいはこれと超臨二酸化炭素（以
下ＳＣ−ＣＯ２という）での抽出除去の組み合わせの処
理を施すことにより、効率よく分離、製造しうることを
見出し、この知見に基づいて本発明をなすに至った。[Means for Solving the Problems] As a result of intensive research conducted by the present inventors to develop an industrial production method of eicosapentaenoic acid from unused seaweed, as a result, among a wide variety of seaweed, The fact that this EPA is present as a major lipid component in the red alga Fudarac, which was not known to contain higher polyunsaturated fatty acids such as EPA,
Then, the eicosapentaenoic acid-containing substance is efficiently separated and produced by subjecting the red alga Fudarac to an organic solvent extraction or a combination of extraction and removal with super subcritical carbon dioxide (hereinafter referred to as SC-CO 2 ). Based on this finding, the present invention has been completed.
【０００５】すなわち、本発明は、紅藻フダラクをクロ
ロホルム含有溶剤で抽出し、次いでこの抽出物からエイ
コサペンタエン酸含有物質を回収することを特徴とする
エイコサペンタエン酸含有物質の製造方法及び紅藻フダ
ラクをクロロホルム含有溶剤で抽出し、次いで得られた
抽出物を超臨界二酸化炭素で処理して非所望分を抽出除
去で減少させ、エイコサペンタエン酸含有物質を回収す
ることを特徴とするエイコサペンタエン酸含有物質の製
造方法を提供するものである。That is, according to the present invention, a method for producing an eicosapentaenoic acid-containing substance, which comprises extracting red alga Fudarac with a chloroform-containing solvent, and then recovering the eicosapentaenoic acid-containing substance from the extract, and the red alga Fudarac. Is extracted with a solvent containing chloroform, and then the obtained extract is treated with supercritical carbon dioxide to reduce undesired components by extraction removal to recover an eicosapentaenoic acid-containing substance. A method for producing a substance is provided.
【０００６】本発明方法において原料に用いる紅藻フダ
ラクは、水洗等で十分に清浄にされ、必要に応じ、破
砕、風乾又は凍結乾燥、これらの組み合わせの処理が施
される。この紅藻フダラクの抽出処理に用いられるクロ
ロホルム含有溶剤として好ましくはクロロホルム−メタ
ノール混合溶剤が用いられる。また、この溶剤での抽出
では、蛋白部や糖部が主に除去され、この抽出操作は低
温で行うのが好ましい。本発明方法は、前記溶剤による
抽出操作だけを行うものであってもよいが、それに続け
てＳＣ−ＣＯ２による抽出除去操作を行うと、遊離脂肪
酸、炭化水素、カロチンなどを相当除去し減少させるこ
とが可能となり、エイコサペンタエン酸分の含有割合を
増大させうるもので一層好ましい。The red alga Fudarac used as a raw material in the method of the present invention is sufficiently cleaned by washing with water and the like, and if necessary, crushing, air-drying or freeze-drying, and a combination of these treatments. A chloroform-methanol mixed solvent is preferably used as the chloroform-containing solvent used for the extraction treatment of the red alga Fudarac. Further, in the extraction with this solvent, the protein part and the sugar part are mainly removed, and this extraction operation is preferably carried out at a low temperature. The method of the present invention may be one in which only the extraction operation with the solvent is performed, but when the extraction and removal operation with SC-CO 2 is subsequently performed, free fatty acids, hydrocarbons, carotene and the like are considerably removed and reduced. It is possible to increase the content ratio of eicosapentaenoic acid, and it is more preferable.
【０００７】また、有機溶剤による抽出処理前に、あら
かじめＳＣ−ＣＯ２抽出に付し、遊離脂肪酸、炭化水
素、カロチンなどをある程度除去することもできる。It is also possible to remove free fatty acids, hydrocarbons, carotene and the like to some extent by subjecting them to SC-CO 2 extraction in advance before the extraction treatment with an organic solvent.
【０００８】[0008]
【実施例】次に、本発明を実施例によりさらに詳細に説
明するが、本発明はこれらの例によって何ら限定される
ものではない。EXAMPLES Next, the present invention will be described in more detail by way of examples, which should not be construed as limiting the invention thereto.
【０００９】実施例１紅藻フダラク２００〜５００ｇを
十分水洗し低温に保ってブレンダーにかけて破片とし
た。この破片は低温下に凍結乾燥し、クロロホルム−メ
タノール（２：１）混合溶剤による抽出処理に付し、得
られた抽出物の抽出溶剤分を留去して、高級脂肪酸含有
固形分を得た。このものの量は約５０ｍｇ／ｇ（フダラ
ク凍結乾燥試料）であり淡い黄色を呈していた。その脂
肪酸組成の分析は常法に従いメチルエステル化したサン
プルをガスクロマトグラフィーに付すことによって行っ
た。その結果を、主な脂肪酸換算組成について全炭素数
と不飽和部分の数により前者：後者の形で示すととも
に、その各脂肪酸の全脂肪酸に対する重量百分率を括弧
中に示すと次の通りであった。１４：０（２．３％）、
１６：０（３４．０％）、１６：１（４．１％）、１
８：１（８．２％）、２０：４（１５．９％）、２０：
５（３５．３％）Example 1 200 to 500 g of the red alga Fudarac was thoroughly washed with water, kept at a low temperature, and then blended to obtain fragments. This fragment was freeze-dried at a low temperature, subjected to extraction treatment with a mixed solvent of chloroform-methanol (2: 1), and the extraction solvent component of the obtained extract was distilled off to obtain a higher fatty acid-containing solid component. . The amount of this substance was about 50 mg / g (Fudarak freeze-dried sample), which was a pale yellow color. The analysis of the fatty acid composition was carried out by subjecting the methyl esterified sample to gas chromatography according to a conventional method. The results are shown in the form of the former: the latter by the total number of carbons and the number of unsaturated moieties for the main fatty acid equivalent composition, and the weight percentage of each fatty acid to the total fatty acids is shown in parentheses as follows. . 14: 0 (2.3%),
16: 0 (34.0%), 16: 1 (4.1%), 1
8: 1 (8.2%), 20: 4 (15.9%), 20:
5 (35.3%)
【００１０】実施例２実施例１で得た高級脂肪酸含有固
形分にＳＣ−ＣＯ２抽出除去操作を施すことによりＥＰ
Ａの高濃度化を行った。すなわち、この高級脂肪酸含有
固形分１０ｇをクロロホルムに溶解し１０〜３５メッシ
ュの海砂に一様にコーティングしたものを抽出槽（１０
０ｍｌ容量）内に入れ、圧力２５．０ＭＰａ及び温度３
１３Ｋに保った抽出槽内へ二酸化炭素を高圧ポンプによ
り１．０５〜３．００ｄｍ３／ｍｉｎの流量で送り込ん
で超臨界状態として２０時間抽出除去し、次いで、抽出
槽から大気圧下にフラッシュさせたガスを分離槽に誘導
し抽出除去物を捕集した。ガス量は積算流量計で測定し
た。抽出除去物は約０．１ｇ／ｇ（高級脂肪酸含有固形
分）であり赤色を呈した。被抽出除去処理物において、
主な脂肪酸換算組成について全炭素数と不飽和部分の数
により前者：後者の形で示すとともに、その各脂肪酸の
全脂肪酸に対する重量百分率を括弧中に示すと次の通り
であった。１４：０（２．４％）、１６：０（３７．１
％）、１６：１（１．７％）、１８：１（８．０％）、
２０：４（７．９％）、２０：５（４０．６％）これよ
り、実施例１の有機溶媒抽出だけの場合に比較してエイ
コサペンタエン酸分を４０パーセント以上の高含量とな
ることが分かる。Example 2 The higher fatty acid-containing solid content obtained in Example 1 was subjected to SC-CO 2 extraction removal operation to obtain EP.
The concentration of A was increased. That is, 10 g of this higher fatty acid-containing solid content was dissolved in chloroform and uniformly coated on 10-35 mesh sea sand, and the extracted tank (10
0ml capacity), pressure 25.0MPa and temperature 3
Carbon dioxide was sent into the extraction tank kept at 13 K at a flow rate of 1.05 to 3.00 dm 3 / min by a high-pressure pump to extract and remove for 20 hours in a supercritical state, and then flushed from the extraction tank under atmospheric pressure. The extracted gas was guided to the separation tank to collect the extract-removed material. The gas amount was measured with an integrating flowmeter. The extract-removed product was about 0.1 g / g (solid content containing higher fatty acid) and was red. In the product to be extracted and removed,
The main fatty acid equivalent compositions are shown in the former: latter form according to the total number of carbon atoms and the number of unsaturated moieties, and the weight percentage of each fatty acid to the total fatty acids is shown in parentheses as follows. 14: 0 (2.4%), 16: 0 (37.1)
%), 16: 1 (1.7%), 18: 1 (8.0%),
20: 4 (7.9%), 20: 5 (40.6%) As a result, the eicosapentaenoic acid content is 40% or more as high as the organic solvent extraction of Example 1 alone. I understand.
【００１１】[0011]
【発明の効果】本発明方法によると血栓症、脳梗塞、心
筋梗塞、血清脂質改善作用や、血液凝固抑制作用などを
有するエイコサペンタエン酸含有物質が、これまで未利
用の紅藻フダラクを原料として簡単な抽出操作で容易に
かつ効率よく工業的に製造することができる。According to the method of the present invention, the eicosapentaenoic acid-containing substance having thrombosis, cerebral infarction, myocardial infarction, serum lipid-improving action, blood coagulation-inhibiting action, etc. is produced from the previously unutilized red alga Fudarac. It can be industrially produced easily and efficiently by a simple extraction operation.
フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ１１Ｃ 1/08 2115−4Ｈ // Ａ６１Ｋ 31/20 ＡＢＮ ＡＢＳ ＡＣＢ 9454−4Ｃ (56)参考文献 特開 平１−294649（ＪＰ，Ａ) 特開 昭62−72793（ＪＰ，Ａ) 特開 昭60−55096（ＪＰ，Ａ) 特開 昭64−79191（ＪＰ，Ａ) 上野誠一著 油脂化学及油脂各論 増補 版 昭和17年12月10日増補第４版 丸善株 式会社発行 Ｐ．468Continuation of the front page (51) Int.Cl. 6 Identification number Office reference number FI technical display location C11C 1/08 2115-4H // A61K 31/20 ABN ABS ACB 9454-4C (56) References JP-A-1 -294649 (JP, A) JP 62-72793 (JP, A) JP 60-55096 (JP, A) JP 64-79191 (JP, A) Seiichi Ueno Oil and fat chemistry and fats and oils Supplementary edition Issued on December 10, 1945, 4th edition, issued by Maruzen Co., Ltd. 468
Claims (3)
抽出し、次いでこの抽出物からエイコサペンタエン酸含
有物質を回収することを特徴とするエイコサペンタエン
酸含有物質の製造方法。1. A method for producing an eicosapentaenoic acid-containing substance, which comprises extracting red alga Fudarac with a chloroform-containing solvent and then recovering the eicosapentaenoic acid-containing substance from the extract.
抽出し、次いで得られた抽出物を超臨界二酸化炭素で処
理して非所望分を抽出除去で減少させ、エイコサペンタ
エン酸含有物質を回収することを特徴とするエイコサペ
ンタエン酸含有物質の製造方法。2. Extracting red alga Fudarac with a solvent containing chloroform, and then treating the resulting extract with supercritical carbon dioxide to reduce undesired components by extraction removal to recover the eicosapentaenoic acid-containing substance. A method for producing an eicosapentaenoic acid-containing substance, comprising:
で抽出する前に、紅藻フダラクにあらかじめ超臨界二酸
化炭素抽出処理を施すことを特徴とする請求項１又は２
記載の製造方法3. The red alga Fudaraku is subjected to a supercritical carbon dioxide extraction treatment in advance before the red alga Fudarak is extracted with a solvent containing chloroform.
Manufacturing method described
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4195829A JPH0765066B2 (en) | 1992-05-28 | 1992-05-28 | Method for producing eicosapentaenoic acid-containing substance using red alga Fudarac |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4195829A JPH0765066B2 (en) | 1992-05-28 | 1992-05-28 | Method for producing eicosapentaenoic acid-containing substance using red alga Fudarac |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06212186A JPH06212186A (en) | 1994-08-02 |
| JPH0765066B2 true JPH0765066B2 (en) | 1995-07-12 |
Family
ID=16347707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4195829A Expired - Lifetime JPH0765066B2 (en) | 1992-05-28 | 1992-05-28 | Method for producing eicosapentaenoic acid-containing substance using red alga Fudarac |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0765066B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002309856B2 (en) * | 2001-05-14 | 2008-10-23 | Dsm Ip Assets B.V. | Production and use of a polar lipid-rich fraction containing omega-3 and/or omega-6 highly unsaturated fatty acids from microbes, genetically modified plant seeds and marine organisms |
| EP1569525A1 (en) * | 2002-11-26 | 2005-09-07 | Phares Pharmaceutical Research N.V. | Marine lipid compositions |
| JP2004201568A (en) * | 2002-12-25 | 2004-07-22 | Shirako:Kk | Blood fluidity improving health food |
| KR101688980B1 (en) * | 2013-08-13 | 2016-12-23 | (주)다인내추럴 | Method for Microencapsulation of Fat-Soluble Materials and Method for Functional Beverage by Using Microencapsulated Fat-Soluble Materials |
| CN107904016B (en) * | 2017-11-10 | 2021-04-20 | 海南华研胶原科技股份有限公司 | Red algae essential oil and preparation method thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6055096A (en) * | 1983-09-06 | 1985-03-29 | 岩谷産業株式会社 | Manufacture of neutral lipid from fishes and shells |
| JPS6272793A (en) * | 1985-09-26 | 1987-04-03 | バブコツク日立株式会社 | Method for concentrating and separating eicosapentaenic acidfrom fish oil |
| JPS6479191A (en) * | 1987-09-22 | 1989-03-24 | Ishikawajima Harima Heavy Ind | Production of fat-soluble component by mass cultivation of order laminariales |
| JPH01294649A (en) * | 1988-05-21 | 1989-11-28 | Agency Of Ind Science & Technol | Method for extracting docosahexaenoic acid and eicosapentaenoic acid in high concentration from spermary of walleye pollack |
-
1992
- 1992-05-28 JP JP4195829A patent/JPH0765066B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| 上野誠一著油脂化学及油脂各論増補版昭和１７年１２月１０日増補第４版丸善株式会社発行Ｐ．４６８ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06212186A (en) | 1994-08-02 |
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